


A Man Walks Into A Bar

by Sammrs



Category: Supernatural
Genre: Alternate Universe, Domestic!Crobby, Established Bobby/Crowley, M/M, Masturbation
Language: English
Status: In-Progress
Published: 2014-02-16
Updated: 2016-11-04
Packaged: 2018-01-12 16:38:57
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 7,657
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1192248
Author URL: https://archiveofourown.org/users/Sammrs/pseuds/Sammrs
Summary: <blockquote class="userstuff">
              <p>Crowley and Bobby own a small but popular bar in Chicago, aptly named "Crowley's". Fifteen years ago, they adopted Dean and Sam after their father drank himself to death, but now, Sam is going through college, Dean tends bar, and life is pretty well normal, until one day, a man walks into the bar and everything changes. (Marked Explicit For Future Chapters)</p>
            </blockquote>





	1. Crowley's Tavern

**Author's Note:**

> Disclaimer: I do not own anything from canon Supernatural. If I did, there would be a lot more canon ships, Charlie would be around more often, and there would have been more M/M naughty bits years ago.

15 Years Ago:

"Crowley, are you sure you can handle this? I've watched these boys their entire lives, and as smart as they are; they're more of a handful than I want to admit." Bobby adjusted his hat, staring at the Englishman before him, "Their daddy never treated them right, with his booze and whatever else he could get his hands on after Mary passed... You're not new to my life, but you'll be new to theirs, and I'm sure they'll go out of their way to give you trouble."

"Robert Singer! How you could ever think I would push aside these boys?" Crowley rolled his eyes as he straightened his suit, "You may as well have raised them, and though I am sure you are correct that they will attempt to give me issues, I've learned all of your tricks, and I'm quite sure I'll learn all of theirs rather quickly. They are still young and I can easily believe that you will be a much better father to them than John Winchester ever was, even if he hadn't drank himself to death."

"I'm just glad he had the sense to make me their legal guardian years ago, so we can avoid the system as much as possible."

"Brutus could use some more socialization as well, so this may help." Crowley shrugged, a small smile gracing his lips.

"Oh that seems smart. Let a four and eight year old boy play around with the damned guard dog. "

"Now now Robert, I'll have you know Brutus can be quite the sweetheart if you give him a real chance."

"Yeah, because the dog who put me in a wheelchair temporarily after our first date is just such a good, kind, animal."

"That was almost a year ago, and besides, he thought you meant to hurt me. He was just a puppy and the poor boy had never heard me in the throes of passion before." His grin grew as the rush of red covered Bobby's face.

Both men sank down to sit beside the sleeping Winchester boys, "We're going to have to make room."

"It's alright Robert, we'll make this happen. We always find a way."

"Thank you... Now, lets get our boys home."

Present Day:

"Dad! We're running low on flavored vodka, schnapps, and we're completely out of bourbon!" Dean Winchester groaned, wiping his hands against his bar apron as he took stock, "We're just lucky we're not out of everything. I still don't get how the end of finals week can cause the need for the amount of booze these kids go through. Tips were nice though."

"How many numbers did you end up with this time Dean?" Crowley rolled his eyes as he jotted down the stock orders, "If you weren't my own son, I'd of probably tried to sell you off to some of those women by now, we'd probably turn quite the profit."

"Six, and you wouldn't dare. Who else would be willing to spend all of their time around you old fools, and tend your bar for this cheap?" Dean laughed, clapping his second father on the shoulder.

"I probably would." A smiling Sam stepped into the room, his school bag heavy on his shoulder, "It'd be a lot easier than law school, and I'd be getting money instead of losing it all the time."

"Have I told you to get a haircut yet today?" Dean grumbled, watching Sam shake his head, "Well get a hair cut Samantha. How was class? I take it not the best in the world since you're talking about bar-tending."

"It's not the law classes, those are fine. It's the elective courses I got stuck taking this year since I ended up being late for registration this year, Dean."

"Woah now, don't go blaming me for that. You're the one who wanted to go to some weirdo summer camp thing to be a counselor." 

"Dean, you slept with six of the other counselors in the three days and then got us lost in the woods trying to escape one of their boyfriends." Crowley laughed from behind the counter, taking up the task of inventory on his own now that Sam was home, "I wouldn't have been late if it wasn't for that."

"Sam, Dean, are you two really arguing about that again?" Bobby had just returned, stepping into the bar from the attached house he and Crowley had built when they married, "Because Sam, a culinary arts course should not be something to complain about. What if you ever decide to bring a woman home again and want to make something for her?

"Dad, cooking wouldn't be bad, but it's a one hundred percent baking course." Sam sighed, sitting down at the bar with his course work, "There is this guy in class, you'd think sweets are all he ever eats. He's always the first to taste test and the last to leave. If that wasn't enough, the professor has decided none of us work in a team well enough and he paired me up with the guy."

"Oh, harsh Sammy. So now you're stuck with the crazy sweets lover and I bet all you want to do is run away with a salad." Dean grinned, argument forgotten, and placed a beer in front of Sam, "Drink up; and don't let it stain the bar top, I just managed to clean the damn thing after the 'dinner' rush."

"We'll just pretend we don't see the illegal drinking going on in our bar." Crowley rolled his eyes and laced his fingers together with Bobby's, "Remember boys, we reopen in 2 hours for the night drinkers, so make sure that's gone before then and you're both ready for the rush." Bobby nodded, and choked back laughter as Crowley began to drag him back into the house, "I'm also sending Brutus over with you two."

"Oh god, couldn't you have just sent him over without warning so we could have just pretended he wandered over on his own? Now I'm going to have to try and burn out the image of Dad-Sex out of my retinas!" With a thud, Dean knocked his head against the bar, "At least we're over here this time."

With a deep woof of protest, Brutus was shoved into the bar; the old Rottweiler immediately flopping his body onto the ground in defeat, "Hey Brutus, how are you today old buddy? I bet you were trying to eat dinner when they sent you over huh?" Sam moved from the bar stool to sit beside their childhood friend, beer still in hand, "I'm sure Dean has a biscuit or something for you behind the bar though; don't you Dean?"

"One step ahead of you Sammy." Within seconds, Dean was beside the two on the floor, a bowl full of dog biscuits in hand, "I've always got something set aside for the best dog in the entire world." He set the bowl down and laid his hand across Brutus' forehead, "So. Tell me more about this new class partner. Is he really that bad?"

"I guess not. He's just so enthusiastic. He's an actual culinary arts major, and he keeps calling me 'Chocolate Moose'. It amuses everyone else and..."

"...And you love it, don't you Sammy? That is why you raged so much over it. You like this guy don't you?" Dean's eyes softened as he stared at his brother, "Let me guess though, straight as uncooked spaghetti huh?"

"I think so. He always jokes around about how he'll get me to play on his side of the street someday, but then he shoves chocolate in my face, so I think he's just joking around about my lack of love for sweets. His name is Gabriel and he's your age I think, but he's so much shorter than me and all I want to do is pick him up, press him against a wall, and---"

"Hey now! I do not need that mental image right now, Sammy." Dean shook his head, "I get it though, you like the guy. Ask him out. What is the worst thing that can happen? He says no? That just means you'll get your closure and wham, you can move on. There is also a chance he'll say yet and you'll have an, apparently cute, man on your arm."

"I suppose you're right Dean," Sam started, "But this doesn't mean you can do the 'I'm always right' dance. We've got to get ready to open back up."

"Aw Sammy, it's just the Friday after finals, what could possibly go wrong?"


	2. I Suggest Stella

**Summary for the Chapter:**

> The first night after finals begins, bringing Sam's crush into the bar followed by a dark haired man who catches Dean's eye and manages to destroy his self control if only for a moment.

**Notes for the Chapter:**

> Masturbation Warning.

In the hour before the bar reopened, Sam and Dean had polished the cherry wood within the bar until it shone, set the steel and leather chairs into place, and restocked to the best of the current stock's ability, but as soon as that open light shone through out the streets, Crowley's became as packed as Wrigley Stadium on opening day, “You alright over there Sammy? Need any help?”

“I've got this Dean, I've been working the tabled since I was sixteen. I just wish you would let me help make drinks.” 

“Sam, you're not quite legal enough yet for us to let you work with the alcohol when the doors are open.” Dean winked and went back to serving, flirting his way into tips and more numbers.

“Well there, I wish I'd of come here sooner.” Sam froze, peering out of the corner of his eye to see the owner of the voice, knowing at the first word who it has been.

“Gabriel. Uh, hey. How are you?” He stammered, awkwardly trying to run his hand through his pulled-up hair, “I've never seen you here before.”

“Well Sammich, I'm an avid bar hopper, but my lovely cousin here wanted somewhere that would not hurt his delicate ears. So we decided to stop here, since I'd never been anyways.” Gabriel hitched his thumb towards the dark haired, serious faced man beside him, “This is Cassie.”

“Gabriel, you know I dislike when you call me that.” The man sighed, holding his hand out for Sam's, “My name is Castiel. It is a pleasure to meet you.”

“Likewise; I'm Sam.” He nodded, “Welcome to Crowley's. My Dad's own the place. Just let me know if you need anything, unless that something is a drink. Then you can go to my brother, Dean. He's the one behind the bar. The dirty blonde one, not the graying one in the cap, that's Dad One-Point-Oh, but you can call him Bobby, the man in the suit is Dad Two-Point-Oh, better known as Mister Crowley.” He rambled on, collecting glasses and bottles from tables as he went.

“It is much appreciated Sam. Gabriel, I believe I will go to obtain a drink so that I can relax for a moment before you start imbibing the liquor and making a fool of yourself.” With that, Castiel stepped away towards the bar and waited for the attention of the, now known as Dean, bar tender.

Dean was keeping up with the orders without issues, until he caught sight of stormy ocean blue eyes and paused. He turned and walked over to the man, enthralled by the messy mop of dark hair, “Hey. I'm Dean. I haven't seen you here before; I'm pretty sure I'd never forget such beautiful eyes.”

“Hello Dean.” He shivered at the sound of his name spoken by the other man's gravelly voice, “My name is Castiel. You are correct though, I have never been to this establishment before, however, I have heard good things.”

“Well, what can I get you then Castiel?” Dean smiled, rapping his hand on the bar softly.

“I will try whatever you can recommend. I am here with my rather... flamboyant cousin, and I would like to be able to survive the night without killing him.” Castiel grinned and laughed slightly and Dean felt his heart nearly beat out of his chest and his cock nearly rip out of his jeans.

“Yeah. Yeah, I can do that.” Dean swallowed and turned, hoping his apron hid his groin until he could take care of it or until the soldier fell down to half mast, “I'll pour you a glass of Stella and we'll see just how you like that.” 

“Thank you Dean.” Dean nodded and poured the drink, handing it to Castiel quickly, “Dad, I'm taking my break, I'll be back in a few, okay?” Bobby nodded as Dean rushed towards the locked door to the apartment he and Sam shared above the bar; making sure to re-lock and deadbolt the door behind him.

“Shit, shit, shit.” Dean growled, throwing himself down on his bed and unbuckling his belt, a small bottle of lube pressed into his other hand, “I am not 14 anymore. I should be able to control myself, not pop a stiffy after looking at a random dude at the bar. I should have at least been able to control myself until the end of my shift when I could take someone up on their offer or something.” He sighed in relief when he pulled his cock from his boxers, slowly covering his hand in the lube and running his hands across the ridges of his own body, gasping slightly as his thumb grazed the head, “If only I could have brought him up here with me, felt the weight of him on top of me. Pressing me into the mattress and letting me sink my teeth into his neck while he fucks me...” He quickened his strokes, twisting his wrist as he played the fantasy behind his eyelids, “Pressing deeper into me as he just fucks me ragged until he screams my name and comes inside me.” At the image of Castiel filling him up, he came, back arching off the bed, muffling his screams with his other arm. 

Downstairs, Sam had began his own break, sitting across from Gabriel and Castiel while they finished their drinks, “So, two dads huh?”

“Yeah...” Sam paused, smiling softly, “When Dean and I were still young, our father died from alcohol poisoning, ironically enough, and Bobby and Crowley took us in. They've been Dad One-Point-Oh and Two-Point-Oh ever since. I was four, and Dean was eight at the time. We've had a good life with them, they built a full house and attached it to the bar and turned the apartment upstairs into first a clubhouse for Dean and I, and then into an apartment again when we were old enough to not get ourselves killed, and responsible enough to not steal from the bar.”

“It sounds as though you have had a very nice life with your family.” Castiel nodded, “I am actually quite jealous.”

“Jealous? Seriously?” Sam cocked his head to the side, “I mean, don't get me wrong, I love my life, but...”

“My family has always been supportive of my education, however, they have never been accepting of my life style. They believe going to school and 'living a more education driven life' will fix me.” 

“When Cassie's parents found out he was gay, it was a bad kind of night. We could hear the screaming halfway down the road at my house.” Gabriel ran his hands through his hair and sighed, “Our entire family went nuts. They've always been extremely religion based and extremely homophobic. Not that I'm saying all religious people are like that, but our family is the kind of religious that condemns everything that wasn't socially normal 100 years ago.”

“Oh that sucks.” Sam's eyes widened, “I can't imagine how much that had to suck Castiel.”

“It was my life, but I believe college is helping me to accept my life style, much to their dismay.” He smiled a little, sipping at his beer, “Your brother has very good taste in alcohol Sam. I am pleased with this 'stella' he poured for me. Though nursing it as long as I have been is diminishing the taste a bit.”

“Yeah, Dean has great taste. In alcohol anyways. He's never had much luck in any other department.”

“Oh thanks Sammy, tell me how you really feel.” Dean stood at the end of the bar, his hair mussed slightly.

“Shut up Dean, you know it's true. What happened, you look disheveled.”

“I took a nap on my break is all.” Dean coughed, “Nothing more.”

“Dean, you took break almost two hours ago. That's a pretty long nap for you when you should be working.”

“Oh c'mon Sammy, bitch face number six? Really? Like you've never taken a long break.”

“Never on the first night after finals I haven't.”

“Alright boys, shut up, both of you.” Bobby barked gruffly from behind the bar, “It's about time we get closed up. Last call; you don't have to go home but you can't stay here!” All four boys laughed as Gabriel stood up.

“We should probably get going anyways Cassie, finals may be over, but we have to start looking for jobs tomorrow.”

“I understand Gabriel. I am quite surprised you have managed to stay as sober as you are.”

“Can't drinky drink when you're too busy talking to a Chocolate Moose.” He winked at Sam and grabbed his jacket, “Nice place though, I'll have to come by more often.”

“Business is always welcome.” Sam coughed, his face blushing profusely, “Uh, but we should all hang out more often?” His voice seemed to raise a few octaves in question, “I mean, I liked talking to you guys, and it's not often I can hold a whole conversation without putting people to sleep.”

“I would like that. I am very much interested in getting to know you and your brother more thoroughly. It has been a long time since I have enjoyed this amount of social interaction.”

“Great! Here's my number kiddo.” Gabriel handed Sam a card covered in doodled lollipops and cupcakes, “Give us a ring when you boys want to hang out.” With handshakes and nods, the four separated.

Once they were out of earshot, Dean shoved Sam playfully, “Look at that. You got yourself a number.”

“Shut up, jerk.”

“Bitch.” The two shared in a laugh and went on their duties cleaning up the bar, Dean teasing Sam throughout the entire night, yet unable to distract himself fully from the thoughts of the dark haired man he hoped to be seeing again soon.


	3. We Need Another Set Of Hands

**Notes for the Chapter:**

> Sorry updates are so far between! I have been throwing a lot of ideas back and forth and it's hard to keep them all in the right place. This is a nice, simple chapter that gives us a lot more detail into the boy's apartment.

“So. Have you called him yet Sammy?”Dean chirped; causing Sam to scoff at him once again.

“Dean, you've been asking me every day this week if I had called Gabriel yet. The answer is still no. Why do you care so much anyways?” He threw his hands into the air, trying to understand his brother. He had not hassled Sam about something like this since he was in middle school, when all he wanted was to ask Amy Pond to the spring dance, but even it had not been this bad. 

“I just want you to be able to get a little some-some is all! You like the midget right?” Dean coughed, looking up at the ceiling of the bar; hoping Sam would not notice the slight tinge of red on his cheeks, “Plus, you know, his cousin there said he wanted to hang out too.” Sam turned his head and tried to fight back his laughter.

“So, see, you don't really want me to call for me. You want to go after Castiel.” Sam winked, leaning against the bar with and placing his head in his hands childishly, “So, why don't you call then.”

“I am not the one who got a number, so stop trying to change the subject Sammy.” Dean shook his head, “Man though, those eyes. They're like an ocean after a winter storm on a moonlit night.”

“That was... almost poetic Dean. Seriously. I didn't know you had it in you.” Both boys jumped at the sound of the thick English brogue, “Really, I didn't.”

“Jesus Christ Dad, you almost gave me a heart attack!” Dean stammered, trying to bring back some semblance of pride into his voice, “It's not nice to sneak up on your kids like that.”

“Oh Dean, if you only knew half of the things I had heard you say. I could make a sailor blush.” He patted Dean on the shoulder and sat down at one of the bar stools, “Now boys. Your father and I have been talking. We would like to bring on some extra hands, just part time. Robert and I would like to be able to take some time off and vacation, and you're both old enough to handle this place on your own, but you do not have enough hands to handle the bar, keep the place clean, and handle the accounting. So, we're going to be completing interviews tomorrow. We would like you boys to do the initial interviews and then send them to Robert and myself if you believe they will be good candidates. We will be closed tomorrow for these, so no partying tonight or excessive drinking or...” He paused, staring at Dean, “Random hookups or Star Wars marathons.”

“Hey now! That last one is unfair! It's a Wednesday night, you know I always watch episodes four, five, and six from approximately eight at night to four am, taking into account bathroom and food breaks. I have a routine!”

“Well tonight, you're going to have to alter that routine. Robert and I will not be around forever, and one day this bar will be yours. We would be more comfortable retiring if we knew you would be ready and able to handle this on your own. So you are going to need to take some responsibility.”

“Fine.” Dean growled, throwing his bar towel down, “I will skip my routine that I have had since I was sixteen so we can prove we're responsible and get some more help around here.”

“Thank you Dean. Now, what we are looking for will primarily be bar hands. We figure two will work, since it's normally you boys and either Robert or myself, this way we're keeping costs essentially low so we won't lose too much money. Sam, we know we can trust you to handle the accounting, and Dean we know you can handle all of the inventory and such, so...”

“Dad, we get it. Relax.” Sam smiled and clapped his hand onto Crowley's shoulder, “We can take care of everything. Do you have interviews set up already?”

“No, we put out for open interviews through the college, for students who have time after class. The deal is, so long as the students keep their grades up, they can stay. If the school finds their grades slipping, they are allowed to pull our workers. However, part of their paychecks will go towards any student loans and such they may have.” Both boys nodded, trying their best to focus on what their father was saying, “So. Yes. I have taken up enough time, you two enjoy the rest of your evening. Robert and I are taking control of the bar for the night. Open interviews open at eight in the morning tomorrow, so get some rest.”

“Alright. Thanks Dad. Don't kill any of the college kids for messing with your suit. Remember, you can only kill them once, you can imagine it forever and avoid jail time.” Dean smiled, walking with Sam up the stairs into their apartment.

Their home was simple in design; an open floor plan affair that made the apartment seem cozy but not catastrophically small. A simple, yet up to date kitchen with white granite counter tops that shone in the morning's light through the large windows that surrounded the walls, cherry wood flooring encompassed the entirety of the space, beyond the bedrooms which were covered in a white plush carpeting. The furniture was sparse; a black leather sectional separated the glossy white-wood coffee table and entertainment area from the small, four person dinning room table. Few photos covered the walls surrounding the television of the boys and their dads over the years, and simple red curtains framed each of the windows throughout the area.

The bedrooms were a completely different story. Sam's contained handmade bookshelves, full to the brink, with the California king sized bed frame built in. It was clean, but sparsely decorated. Dean's room was nearly the opposite; full of band memorabilia and enough geek merchandise that some may thing that Comicon has vomited and not taken the time to clean up it's own mess, as well as a large wrought iron, king sized bed.

“Sammy, you think the Dads are really thinking of retiring already? I mean, I get they're older, but I can't imagine either of them not working...”

“They probably just want to prepare us Dean, and want to prove to us that we can handle this on our own anyways. When was the last time they took a vacation, without us, that lasted more than a day?” Sam shrugged, sitting down at the dining table, “Besides, wouldn't you like to have a day off once in a while?”

“I guess.” Dean grumbled, searching through the fridge for something to eat that would allow him to avoid cooking, “So, popcorn for dinner? I don't really want to cook, and I wasn't expecting to be home to make a real meal, so nothing is thawed.”

“Popcorn is fine Dean. Do you want to watch Star Wars anyways? We can get through at least two of them and get enough sleep to interview without any problems since we're having easy dinner anyways.”

“Awesome. Set up the DVD player Sammy, I'll get the popcorn popping.” Dean laughed, “Let's go with Empire Strikes Back and then bed. I can't watch two and not watch the third one too, it'll be too weird.”


	4. Interview Day

**Summary for the Chapter:**

> Dean and Sam have to conduct interviews to find new help around the bar so their Dads can go on vacation for once, will they manage?

**Notes for the Chapter:**

> Hello and welcome to another installment of "A Man Walks Into A Bar"! This would have been updated sooner, but my computer decided it needed a good old fashioned restore a while back and I didn't realize I had lost it. 
> 
> Anyways! Enjoy!

“Sammy, I can't take it anymore.” Dean groaned, pouring himself a shot behind the bar, “We have been interviewing for almost seven hours and if I hear one more person ask if they get to drink for free when they work here, I am going to explode!” 

“Think of it this way Dean, at least you didn't have someone grab your...” He flailed his hands near his groin, “Multiple times.”

“Hah, yeah, that was funny though.” Sam glared back at his brother, “Oh c'mon Sammy, not bitch face number 16!” He clutched his chest as he knocked back his shot and feigned sorrow.

“Maybe we won't have anyone else come through.” Sam dropped his head into his hands, “Or maybe we'll at least get someone competent. I mean, how hard is it to find two people to help around in a bar? It's not a minimum wage job, we'll be flexible with hours...”

“Did I hear someone say flexible hours? Also, knock knock!” In the doorway stood Gabriel, as well as a confused looking Castiel, grin plastered on his face, “Chocolate Moose! You never called me, I got depressed.” His grin seemed to widen as he watched Sam's face flush, “Oh well, you'll have to go out to dinner with me to make it up to me. Sound good? Six tomorrow? Great it's a date!”

“Uh, okay.” Sam's eye widened as he nodded, unsure if this was actually happening or if he had fallen into the rabbit hole and into wonderland without knowing it.

“Gabriel. I believe we were here for more reasons other than for you to just harass Sam?” Castiel said pointedly before realizing he was being impolite, “Hello Dean. Hello Sam.” 

“Hey Cas!” Dean put his head in his hand, “Oh, it's probably a bit early for nicknames huh? Only met you once.”

“Actually, I think Cas would suit me fine. Much better than 'Cassie' as Gabriel still insists on calling me.” Castiel nodded, thinking about his newly given moniker, “Ah, however, we are here on business technically. Have you hired your bar hands yet?”

“No!” Both Sam and Dean answered in unison.

“We haven't! I completely forgot you had mentioned you two were on the hunt for jobs.” Sam and Dean both looked as if the weight of the world had been lifted from their shoulders, “You two sure you can deal with working in a bar?”

“So long as the hours are flexible around classes, I believe so. May I sit?” Cas pointed to a bar stool near Dean and he nodded before Cas could complete his sentence, “Thank you. As I was saying, Per your hours of operation, I would be in class during the night rush on most week nights, but I am free on weekends, and I know Gabriel's schedule is near opposite mine.”

“Yeah. Crazy how when you want to bake they expect you to be up early all the time. I mean, couldn't I have a night bakery? Seriously.” Gabriel rolled his eyes before winking in Sam's direction, “I am also free on the weekends and don't mind standing for hours on end.”

“I also took a bartending class my first semester. I have all of my information here.” Castiel pulled two perfect looking resumes from his trench coat, “Gabriel, I also took the liberty of refreshing your resume and bringing it along.”

“Thanks Cassie.” 

“Please do not call me that.”

“Oh poo on you, party pooper.”

“Gabriel.”

“Oh fine. I'm sorry.” He snickered a little bit and looked between Sam and Dean, “Well, what do you two say? Do we have the jobs?”

Dean waved Sam over and they looked at the resumes together. Gabriel was indeed a culinary arts student, age twenty three and well on his way to graduating with honors within his program. Castiel was twenty one and a creative writing major with more minors than the two boys cared to count. Neither had too much work experience, but appeared to have gone to college as soon as they had graduated high school, “Alright. We'll take you two on a trial run this weekend. You survive working with Sam, the Dads, and Me, and you're in.”

“You'll come in at two in the afternoon and stick around until two in the morning when we close up. Obviously there will be breaks and lunches and we have two hours between the early drinkers and the night owls to clean up shop and get ready. During the earlier hours, we serve food, kinda, but when we close for the in between, no more kitchen items, mostly because no one wants to go use the Dads kitchen after 10pm and end up accidentally walking in on them.” Sam coughed, trying to block out the mental images of the last time he attempted to use their kitchen at night.

“Also, you'll have to deal with Brutus. He's a good old guy, but if there is any funny business he will be the first to latch onto your ass and not let go. No joke. He may be old and running out of teeth, but he'll leave them in your ass if he thinks you've done something horribly wrong.” Dean smiled, looking to Gabriel periodically, but mostly keeping eye contact with Castiel who seemed to be paying more attention than Dean thought he would, but he nearly laughed when Cas raised his hand mid spiel.

“Who is Brutus and why would this man want to bite our hindquarters? Does that not seem unsanitary? Maybe he should be made to retire.”

“Oh man, no, Brutus isn't...” Sam and Dean laughed, pushing open the door between the bar and the house, “Brutus, come here!” Dean knelt down with his arms open, hugging the old dog as he pawed his way slowly towards them, “There's a good Brutus. Good dog.” 

Sam patted him on the head and turned back to the others, “Brutus is, what, like seventeen? Something like that. Either way, he's been around forever, and he likes to stick behind the bar and keep us company. He's also the guard dog and the only security system we've ever really needed.” 

Castiel slipped off the bar stool and knelt down beside Dean, holding out his hand for Brutus, “Hello Brutus. My name is Castiel and I will be, hopefully, engaging in work within your establishment. I hope you and I will work well together and that you will refrain from putting your teeth into my backside.” Brutus sniffed the hand for a moment before placing his own paw onto it and licking his way up Cas's face, “I believe I may have just been accepted?”

“Oh man Cas, your face is covered in drool.” Dean laughed, grabbing a towel from his apron and clearing off his face, “Uh... Sorry. Personal space huh?” Cas's cheeks glowed as he shook his head.

“It is alright. I, uhm... Appreciate the gesture.” He looked away from Dean, trying to calm the blood flow to his face and the sudden racing of his heart, “Gabriel, are you going to come and introduce yourself to Brutus? We are guests and you should respect your elders.”

Gabriel rolled his eyes halfheartedly, but approached Brutus, “Wow, you're huge. You'd probably eat my terrier, Cookie. I'm Gabriel, and I am not really sure why I am talking to a dog, but hey, if you're gonna be one of my bosses, and the head of security, I might as well make an impression.” He pulled a peanut butter bar out of his pocket and held out half to Brutus who gladly scarfed down the treat, tail pounding against the floor.

All four boys laughed as Brutus clamored closer to Gabriel, hoping for more. This appeared like it was going to be the start of an amazing friendship.


	5. Sam And Gabriel's First Date

**Summary for the Chapter:**

> As the time comes for Sam and Gabriel's first date, Sam begins to panic.

**Notes for the Chapter:**

> Sorry that updates have been so far between. I promise I'm trying. Work has been hectic and life even more so. I'm moving again in June, so I am hoping to get as many updates as possible done before that since I don't know how long I will be without internet. Anyways! Enjoy Sam and Gabriel's first date. :D

Dean and Sam had sent Castiel and Gabriel to their fathers and were very pleased to hear they had both aced the final interviews that Friday morning, meaning they would be showing up for work that Saturday. However, Sam had other things on his mind.

“Dean what the hell should I wear?!” He groaned. His normally immaculate room was covered in clothing and his closet stood empty, “I mean, should I dress up? Is this a casual thing? Is he even going to really show up?!”

“SAM!” Dean shouted, rubbing his fingers against the bridge of his nose, “Will you calm down, please? He didn't mention anything over the top, so don't go over the top. Assume it is a casual situation until otherwise noted, and for gods sake, he is the one who asked you on the date, so I am pretty sure he is going to show up. It's only 5, and he said 6. So, again, calm down and wear the light wash jeans with the dark button up and the dark-ish belt. Don't try and ask me about the shoes though, I have no idea on that one. Not my thing.” Sam took a deep breath in an attempt to calm himself before sitting on the end of his clothing covered bed next to Dean.

“Sorry Dean. I'm just a little frazzled.”

“A little? Really. I couldn't tell.” Sam punched him softly in the arm, “Bitch.”

“Jerk.” 

~

Six O’clock came and, without missing a beat, there was a knock on the outer apartment door. “Hey there Sam.” Gabriel grinned, staring up at the taller man as if he were the cat who stole the canary, “You look awesome.”

“Thanks Gabe.” Sam coughed, a light blush crossing his face, “You do too. I'm not... under-dressed or anything?”

“No, not in the slightest.” His words were soft as he placed his hand on Sam's arm, “C'mon, lets go.”

He led Sam to a small truck and it finally occurred to Sam he had never actually seen Gabriel's vehicle. He had just kind of assumed he popped up wherever he needed to be, knowing it was an inaccurate assumption, but fantasizing on that basic idea on far more occasions that he cared to admit, “Nice truck.” Sam managed to choke out, trying to force his mind to drift away from the thought train he was on before he had to make a hasty exit. 

“Thanks, she gets me where I need to go.” His smile never wavered as he kept his eyes on Sam, “Climb on in, it's not a long drive.” 

Gabriel and Sam chatted about class during the brief ride, until they reached a small house outside of campus. When Gabriel parked, Sam looked at him quizzically.

“You'll see. Come on, lets go inside.” Gabriel's eyes sparkled with glee as he led Sam into the house, “Keep your eyes closed!” 

“They're closed, they're closed.” Sam laughed, letting Gabriel direct him. He heard the soft click of an unlocking door and the scamper of tiny feet as he was led through the building and finally seated.

“You can open your eyes now.” Gabriel's voice was triumphant as Sam began to open his eyes. The table in front of him was well set with a crisp red table cloth and white dishes. Dishes of mixed greens and mashed potatoes sat beside what appeared to be a roasted chicken, “I may be going through school for baking, but I can cook too. I hope you like it.” He sounded proud and yet he seemed frozen in anticipation.

“It's amazing Gabe. This is already the best first date I've ever had.” Sam smiled, pausing to look down as ten tiny claws dug into his leg, “And who is this?”

“Oh, that's Cookie. She's a rat terrier I adopted a few years ago. She's almost completely blind, so she tends to jump and sniff a lot, but she's a doll.” 

“She looks like a little frosted cupcake.” 

They shared a laugh and Gabriel pulled out a chair for Sam, “Take a seat, we don't want the food to get cold. Cookie, down sweetie.” The dog's ears perked and she sat down on the floor, waiting for the inevitable scrap from her fur-dad.

The two gentlemen ate silence, sharing a smile from time to time, just enjoying the others company. When the mean was done, Sam was the first to speak. “So, since you made the meal, you should at least let me do the dishes.” Gabriel almost choked on his drink.

“No, no. You don't need to do that. I've got a dish washer in the kitchen and---”

“Alright, I'll load the dish washer then.” Sam laughed, picking up the empty dishes from the table, “You cooked, it's the least I can do after such a wonderful meal.” Gabriel watched as Sam finished picking everything up and found his way around the kitchen to find the dish washer and soap. Gabriel closed his eyes and smiled, listening to Sam hum as he worked; enjoying the sound of someone other than himself or Castiel within the household. 

“Thanks for joining me Sam. I may not have seemed like it, but I was terrified to ask you out. Beyond terrified.” He threw his hands into the air for a moment, “I mean, seriously. You could have any person you wanted. I mean, you probably don't notice since you're usually face first in a book, but people of every gender in the spectrum keep trying to throw themselves at you.” Gabriel mashed his hands together to mimic a bunch of people throwing themselves at Sam's face.

“Hah, yeah, no. Even if that was true, I would never have noticed it.” Sam bit his lip softly, “I didn't have eyes for anyone else except you, but I was so very sure you were straight that I pretty much just moped around.”

“Let me tell you, pansexuality is a fantastic thing.” He stood up and walked into the kitchen, leaning against the counter so they could speak face to face.

“I guess so.” Sam grinned, leaning down to press a soft kiss against Gabriel's lips. “Also... I'm glad you asked me out, too.”


	6. It's Off To Work We Go

**Summary for the Chapter:**

> The first day on the job has come; can Gabriel and Cas handle the Winchester training regiment?

Finally, Saturday arrived. The first morning of training, and the first contact after Sam and Gabe’s first date. “Hey! Good to see you two here bright and early. We’re going to split up the training throughout the day. We’ll start with two hours now, before we actually open. You two will be tending the bar, but we want to make sure you know all aspects of the place, just in case something happens.” Dean smiled, stretching out behind the bar, “You two can chill here with us in the apartment, if you like, until we open for lunch. We don’t make much in the way of food at the moment, even though The Dad’s really want to start doing so; but we do serve beer and wine from noon to four with little things like popcorn and pretzels.”

“To be honest, the early afternoon hours are generally meant for the students who don’t want to hit up the library or sit in their dorm rooms and study.” Sam remarked offhandedly, moving to stand beside Gabriel, “It gets really hectic during that time frame though, especially during or right before exams. We’ll be hitting the slow afternoon season soon, but nights are almost always packed on the weekends, so we’ll have plenty to do.”

“Sam is right in that. Back on the training schedule though, so we can get it out of the way. After lunch, we’ll take another break and then you two will shadow us for the rest of the night. Since he is already glued to his side, Gabe can shadow Sam and bus tables tonight. Cas, you’ll be with me behind the bar. Half way through the night, we’ll swap your places and finish off the night. If you two are comfortable with the basics, we’ll watch you two tomorrow night and only step in if you need us.”

“Sounds good to me.” Gabriel happily signaled his acknowledgement with a thumbs up.

“I agree. I think knowing each ‘station,’ so to speak, will make it easier to complete any work, should we fall behind during a busy night.” Cas nodded, “So, where should we begin?”

“We will start with inventory! Let’s check the stock at the bar first, and then head down into the cellar to check stock and see if there is anything we need to bring up or order more stock of.” Dean pulled a clipboard out from under the bar and slid it over to Cas and Gabe, “This part is easy. Everything we have at the bar already, jot down a ‘b’ with the number of bottles currently out. If you don’t see a bottle that is on the bar list, at the actual bar, leave the box blank.”

Dean stepped back and stood with Sam as they watched Gabe and Castiel work together to list all of the bottles at a decent pace; just quick enough that they wouldn’t be wasting time, but slow enough to make sure they were doing the work properly.

“Does this look alright, Dean? Sam?” Cas smiled and handed over the inventory clipboard for assessment.

“Looks good to me. What do you think?”

“Seems like everything is there, Dean. Let’s hit up the cellar.”

After moving the safety matting from the floor behind the bar, Sam slid open the cellar door and walked down the slim steps, closely followed by the other three men. “The cellar is a pretty simple place, just like the bar. The marks are the same style as upstairs, just use ‘c’ instead of ‘b,’ and mark for the number of bottles. If there are less than 6 bottles of anything, and that is after you move product from the cellar to the bar, make sure to highlight it so we know it needs to be ordered. Pretty simple all and all.” Gabriel and Cas started going through the crates as Sam continued, “We just did a bar fill yesterday though, so keep in mind that it is normally not this cluttered… When you have to bolt down here during a rush and grab bottles though, it tends to throw all of The Dad’s organization out of whack. So, take your time, because you’ll you’ll be down here every day, at least once.”

“Before open and after close, right?” Gabriel craned his neck back a little bit, making sure he did not write down the wrong information, “That’s pretty smart. Not just because you always know what is here, but you can watch trends and see what people like.”

“That is right.” Dean nodded, “I always figured they did it to make sure Sammy and I weren’t sneaking drinks as kids, though.” Everyone laughed; and upstairs Bobby smiled a little. He was very happy that, not only did his boys appear to be working well with the new workers, but the business would be in good hands when they finally did tell the boys of their retirement plans.

The rest of the day flew by; much to Sam and Dean’s dismay. Cas and Gabe had gone to run their own errands between opening and closing training, leaving the others two to wait until they returned. “You know Dean, I really was hoping they would stay… at least this afternoon. I can understand leaving after work though. Would have been nice to be able to just hang out with them a bit.”

“Yeah, that makes two of us, but it isn’t like we won’t see them tomorrow. Plus, I made it so you get to follow around your Candy-Man all day.” Sam rolled his eyes as Dean smirked.

“Oh sure, I am sure it made it so easy for you since you get to follow around Tall-Dark-And-Handsome all day.” Dean’s grin faded as he turned to stare outside their apartment window.

“You’re right. I guess I do.” The silence was almost deafening, “Hey Sammy?”

“Whats up, Dean?”

“Want to watch RENT again and order a pizza?”

“Sure Dean. That sounds like a good end to the night.”


End file.
